I wanna get better at determining when situations require more effort or when they require less effort.

This may be kind of vague but the concept presented here is pretty wide reaching and applicable to many situations.

I overdo things sometimes. I become fixated on looking for things that I can do to improve a given situation. However "doing" is only half of what makes someone successful in any given endeavor. Equally or more important is "not doing". For example you have to know when TO NOT text the girl back, when TO NOT kiss her.

Internally you need to know when you have to push yourself because your being a pussy, but you also need to know the time to slow down and stop trying so hard.

I know one of the answers to this is more field experience as reference, but I know there are also other creative ways to exercise this faculty because it's just such a pervasive part of life.